U.S. patent number 3,970,639 [Application Number 05/615,871] was granted by the patent office on 1976-07-20 for ethyl .alpha.-cyano .beta.-(n-methyl-n-cyclohexylamino) acrylate stabilizer.
This patent grant is currently assigned to American Cyanamid Company. Invention is credited to William F. Cordes, III, Robert E. Diehl.
United States Patent |
3,970,639 |
Cordes, III , et
al. |
July 20, 1976 |
Ethyl .alpha.-cyano .beta.-(N-methyl-N-cyclohexylamino) acrylate
stabilizer
Abstract
Polycarbonate is effectively stabilized against degradation by
ultraviolet radiation by ethyl
.alpha.-cyano-.beta.-(N-methyl-N-cyclohexylamino)acrylate.
Inventors: |
Cordes, III; William F. (East
Brunswick, NJ), Diehl; Robert E. (Trenton, NJ) |
Assignee: |
American Cyanamid Company
(Stamford, CT)
|
Family
ID: |
24467153 |
Appl.
No.: |
05/615,871 |
Filed: |
September 22, 1975 |
Current U.S.
Class: |
524/207; 524/611;
558/430 |
Current CPC
Class: |
C07C
255/00 (20130101); C08K 5/315 (20130101); C08K
5/315 (20130101); C08L 69/00 (20130101) |
Current International
Class: |
C08K
5/00 (20060101); C08K 5/315 (20060101); C08J
003/20 (); C07C 121/00 () |
Field of
Search: |
;260/465D,45.85A,45.85N |
References Cited
[Referenced By]
U.S. Patent Documents
Other References
Index Chemicus, 21, 63462 (1966)..
|
Primary Examiner: Hoke; V.P.
Attorney, Agent or Firm: Mintz; Philip
Claims
We claim:
1. Polycarbonate stabilized against the deteriorating effects of
ultraviolet radiation by an effective amount of a stabilizer which
is ethyl
.alpha.-cyano-.beta.-(N-methyl-N-cyclohexylamino)acrylate.
2. A composition as defined in claim 1 wherein said stabilizer is
present in an amount of 0.1 to 5.0 percent on weight of
polycarbonate.
3. .alpha.-Cyano-.beta.-(N-methyl-N-cyclohexylamino)acrylate.
Description
This invention relates to a novel compound and to its use to
stabilize polycarbonates against degradation on exposure to
ultraviolet radiation.
Polycarbonates can be formed into useful articles, such as pipe,
hollow objects (e.g. bottles, tumblers, etc.), film, sheet, lenses,
hard hats, etc. by such process as injection molding, extrusion,
blow-molding, etc. Because of their desirable properties and ease
of forming into useful articles, polycarbonates have attained wide
commercial utilization. In some of these uses, the polycarbonate is
exposed to ultraviolet radiation, such as in sunlight. As is well
known, such exposure causes degradation of the polycarbonate,
leading to discoloration and embrittlement. It is an object of this
invention of provide a novel compound useful, when incorporated in
polycarbonates, for inhibiting degradation caused by ultraviolet
radiation.
In accordance with the present invention, it has been found that
ethyl .alpha.-cyano-.beta.-(N-methyl-N-cyclohexylamino)-acrylate
having the formula: ##EQU1## is effective for inhibiting
degradation of polycarbonate on exposure to ultraviolet
radiation.
This compound may be incorporated into polycarbonate by any of the
standard techniques, including milling, screw extruding, Banbury
mixing, swelling, etc. This compound is effective over a wide
concentration range of about 0.1 to about 5.0 percent based on
weight of polycarbonate. Preferably, it is used at a concentration
of about 0.5 to about 2.0 percent on weight of polycarbonate. Other
additives, such as dyes, foaming agents, pigments, plasticizers,
thermal stabilizers, etc. may also be added to the polycarbonate
for their usual functions.
This invention is further illustrated in the following examples,
wherein all parts are by weight unless otherwise stated.
EXAMPLE 1
A mixture of 7.21 grams (0.064 mole) of N-methyl-N-cyclohexylamine
and 10.3 grams (0.07 mole) of triethyl orthoformate was heated to
105.degree.C. and 6.9 grams (0.06 mole) of ethyl cyanoacetate was
slowly added thereto. The temperature gradually rose until ethanol
began to distill over. After 11.4 milliliters of distillate was
collected, the reaction mixture was cooled to room temperature and
poured into water. The aqueous mixture was extracted with diethyl
ether, dried over anhydrous magnesium sulfate, and evaporated to
obtain 14.0 grams of a dark oil. The oil was heated under vacuum to
remove some distillable material and the remainder was extracted
with three portions of hot cyclohexane which, on cooling, gave a
total of 5.7 grams of light tan powder. The powder was
recrystallized from cyclohexane, yielding 4.0 grams melting at
65.degree.-70.degree.C. Further recrystallization from petroleum
ether gave ethyl
.alpha.-cyano-.beta.-(N-methyl-N-cyclohexylamino)acrylate as fine
white plates, melting point 71.degree.-72.degree.C.
Analysis: Calculated for C.sub.13 H.sub.20 N.sub.2 O.sub.2 : C,
66.07; H, 8.53; N, 11.86 Found: C, 65.98; H, 8.54; N, 11.72.
EXAMPLE 2
A test film was prepared by adding the stabilizer, ethyl
.alpha.-cyano-.beta.-(N-methyl-N-cyclohexylamino)acrylate, to a ten
percent solution of water-free unstabilized polycarbonate in
chloroform, casting, and drying at 2.degree.-25.degree.C. to obtain
a film one mil thick. The quantity of stabilizer added was one
percent on weight of polycarbonate. The film was exposed to
ultraviolet light in an Atlas Xenon Weather-Ometer (no water spray
in the Weather-Ometer) until it became embrittled to the point of
complete destruction. The efficiency of the stabilizer in
preventing degradation is measured in terms of the time in hours to
failure of the film over a control sample which contains no
stabilizer. This film showed an increase of 2500 hours to failure
(a 166% increase) compared to a control film without
stabilizer.
* * * * *